Triethylamine → N-tert-Butyl-3-((4-(4-(cyclohexanecarboxamido)-3-fluorobenzoyl)piperazin-1-yl)methyl)-benzamide

HRID 1878327Notes

Reaction equation

HRID 1878327 reaction equation
[NH2:1][C:2]1[CH:29]=[CH:28][C:5]([C:6]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=3)[C:18]([NH:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:10][CH2:9]2)=[O:7])=[CH:4][C:3]=1[F:30].C(N(CC)CC)C.[CH:38]1([C:44](Cl)=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>ClCCl>[C:21]([NH:20][C:18](=[O:19])[C:17]1[CH:25]=[CH:26][CH:27]=[C:15]([CH2:14][N:11]2[CH2:12][CH2:13][N:8]([C:6](=[O:7])[C:5]3[CH:28]=[CH:29][C:2]([NH:1][C:44]([CH:38]4[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]4)=[O:45])=[C:3]([F:30])[CH:4]=3)[CH2:9][CH2:10]2)[CH:16]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 668785283-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide

Product 1

HCID 57917706N-tert-Butyl-3-((4-(4-(cyclohexanecarboxamido)-3-fluorobenzoyl)piperazin-1-yl)methyl)-benzamideYield 44.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3-((4-(4-amino-3-fluorobenzoyl)piperazin-1-yl)methyl)-N-tert-butylbenzamide (0.121 mmol, 50 mg) and triethylamine (0.485 mmol, 0.068 mL, 49.1 mg) in dichloromethane (1.5 mL) was added cyclohexanecarbonyl chloride (0.133 mmol, 19.55 mg). After 16 hours stirring, the reaction was concentrated under vacuum and purified by acidic reverse phase HPLC to yield the title compound (28 mg).

Workup

  1. concentrationthe reaction was concentrated under vacuum
  2. custompurified by acidic reverse phase HPLC

Sources & evidence

ORD record
ord-75f195a946074e249d471db0593f82bf
Source dataset
uspto-grants-2012_11
Patent number
US08314091B2

Reaction notes

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